The Eastern Shore
In researching the trip, we’d received a few outlandish suggestions, but one place popped up on everyone’s itinerary: St. Michaels. It was made out to be the Holy Grail of Maryland’s Eastern Shore, and we all agreed it was a must. The easterly breeze made getting there tricky, but we slowly made ground upwind, across the bay and around Love’s Point, where we bore off and sailed south for Kent Narrows.
The drizzle returned, and the temperatures refused to rise, so the crew played cards in the cozy saloon while my first mate, Matt, and I sat cheek-to-cheek at the helm, trying to stay warm. By now we had discovered that navigating the bay requires vigilance both below and above the boat: below, mind your draft over the shoals that seem to materialize from nowhere; above, mind your clearance for the just-tall-enough bridges, such as the one at Kent Narrows.
We anchored in St. Michaels at 1300, and by 1430 we’d already decided to stay two nights. It was evident we’d need at least that much time to soak up the unique subculture of the Eastern Shore—the rich maritime history, the modern-day charm, the friendly people and the natural beauty. Besides, the sun was threatening to break through as we took the dinghy ashore, and we wanted to enjoy as much of it as we could.
“Eight Rusty Rockets, coming right up!” By 1600, the crew was seated at a bar at 605 S. Talbot Street, home of the Eastern Shore Brewery, where owners Ace and Lori welcomed us in for a tour and a sampling of their art. Rusty the bartender poured a round of his namesake shots to kick things off: one part India pale ale, one part Tabasco sauce and one part secret ingredient that sets your lips on fire.
The brewery—the only on the Eastern Shore—began a few years back when Ace and Lori decided to quit their jobs and follow their dreams. It has since blossomed into a serious operation with rooms for growing hops, brewing and bottling their four delicious signature brews. Like so many of the people we met in St. Mikes, Ace and Lori could have entertained us for a long while, but the rest of the Grail called.
Our next stop was the Maritime Museum, where roomfuls of displays bring the history of the Chesapeake Bay to life. The first people to populate the area came 12,000 years ago, and the first European settlers landed here in the early 1500s, flying the flag of Spain. After that came French and then English explorers who in 1607 founded Jamestown, the first permanent English settlement in North America.
For centuries after, oystermen and fishermen made their living on these waters, modifying their practices and boats to meet the changing needs of their nascent country. In that sense, the bay is a birthplace of America, and the Maritime Museum, with its photos, ships, lighthouse and artifacts, is a tribute to that story. It’s a must-see on any Chesapeake charter as it puts into perspective the generations of sailors who’ve plied these waters before you.
It was now mid-week and spring was finally emerging from her cave. We stripped off layer after layer of outerwear as we sailed to Oxford. The breeze also became stronger, blowing 15 knots on our starboard shoulder as we made our way down and around Tilghman Island into Oxford Marina. By the time we got there it was gusting to 30 knots, so we were happy to tie up to the docks for the night.
Like St. Michaels, Oxford is a small town full of friendly people and pretty roads for biking. We had only one mission in mind: Maryland crabs, and lots of them. Crabs are to the Chesapeake as chowder is to Boston and gumbo is to New Orleans, and we had yet to indulge. Matt, Tyler, Teresa and I rented bikes from the marina and rode to The Pier Restaurant where the bartender gave us four dozen crabs, a lesson in crab-eating and enough Old Bay seasoning to flavor our next 30 meals. We loaded everything into the bike baskets and zoomed back to our hungry crew who had already sheathed the settee table with newspapers. The next few hours were more of an operation than a meal. With mallets flying, crab legs cracking and Old Bay sprinkling, we worked our way through the mound of crabs, eventually collapsing in a collective food coma. The Eastern Shore is delicious.
The Western Shore
On the penultimate day of our trip, it finally felt like spring. Temperatures rose to the 70s and that reliable eastern breeze propelled us back across the bay, through Knapps Narrows on Tilghman Island and into Herring Harbor on the Western Shore. Though a mere 25 miles separates the two shores, it felt as though we’d entered an entirely different world. With no town to speak of, Herring Harbor’s claim to fame are its massive boat storage facility and Mango’s, its slightly out-of-place Caribbean-themed tiki bar. The only thing better than the people-watching was the boat-watching: over a mile of docks housed everything from little old wooden sloops to massive powerboats.
As is often the case, our final day was warm—really warm—so we took our sweet time sailing back to Annapolis. Along the way, we stumbled upon another regatta, dropped the sails and drifted behind the starting line. Tyler rigged a hammock, Matt brought out a guitar and we provided our own race commentary for the fleet of J/22s.
For a crew of sailors accustomed to over-planning our vacations together, it was a bit nerve-wracking to arrive in the Chesapeake with such a blank canvas. Luckily, in a region full of such beauty, history and diversity, it’s hard to go wrong.